HCID 18362931, compound → HCID 18362947, compound

HRID 1276688Notes

Reaction equation

HRID 1276688 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]#[C:6][C:7]1[N:8]([CH2:23][C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:27]=[CH:26][CH:25]=2)[CH:9]=[C:10]2[C:15]=1[C:14](=[O:16])[N:13]([CH3:17])[C:12](=[O:18])[N:11]2[CH2:19][CH:20]([CH3:22])[CH3:21].[H][H]>C(O)C.[Pd]>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[N:8]([CH2:23][C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:27]=[CH:26][CH:25]=2)[CH:9]=[C:10]2[C:15]=1[C:14](=[O:16])[N:13]([CH3:17])[C:12](=[O:18])[N:11]2[CH2:19][CH:20]([CH3:22])[CH3:21]

Participants

5

Reactant 2

HCID 18362931HCID 18362931, compound2×HCID 178418361HCID 178418361, compound

Product 1

HCID 18362947HCID 18362947, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

The compound of Example 13, 5-(5-hydroxypent-1-ynyl)-3-methyl-1-(2-methylpropyl)-6(1-naphthalenylmethyl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (75 mg) was suspended in ethanol (50 ml). A suspension of 10% palladium on carbon (7 mg) in ethanol (3 ml) was added and the mixture was hydrogenated. When hydrogen uptake ceased, the reaction mixture was filtered and the solvent was removed by rotary evaporation. The crude product was purified by chromatography on silica eluting with ethyl acetate:isohexane (3:1) to give the title compound (29 mg) as an oil.

Workup

  1. additionwas added
  2. filtrationthe reaction mixture was filtered
  3. customthe solvent was removed by rotary evaporation
  4. customThe crude product was purified by chromatography on silica eluting with ethyl acetate:isohexane (3:1)

Sources & evidence

ORD record
ord-6033e34088e249819f2811f5c61ddb84
Source dataset
uspto-grants-2000_12
Patent number
US06166206

Reaction notes

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